Fluent in the Tools, Illiterate in the Tradeoffs — Frank Bravo on AI's Real Risk

0:00 SPEAKER_01: Most organizations are not behind on AI. They are behind on the thinking required to use it. I am Arnan Sapatnaik, ex-Microsoft Data and AI executive, CEO of Tipsora, and your host. This is what comes next, the podcast where we talk about building the kind of organization that actually wins in an intelligence-driven economy. Let's get into it.

0:51 SPEAKER_01: He served more than 30 years as CTO of Embarcadero Media in Palo Alto, home to the Palo Alto Weekly, guiding the organization through the full print to digital transition. He currently serves as CTO of Troll Legal, a legal services startup, and is principal of Bravo IT consulting in San Carlos, California. He is also the host of Your Tech Makeover, a podcast that turns confusing technology into clear practical guidance for people who don't consider themselves technical. That translation work is the through line of his career.

1:38 SPEAKER_01: Frank spends his time on both ends of the spectrum, with the executives deciding what technology to adopt and with the people who actually have to live with those decisions. So with that, Frank, welcome to the show.

1:54 SPEAKER_00: Thank you. Great. Thanks for having me. I appreciate it.

1:58 SPEAKER_01: Yeah, uh, we didn't get to talk much before the show, but uh I I am author of a book called Future Proof Your Business, where I talk about my framework for building a scalable success. So the framework has five stages find your nest, you know, see what you can do that others would find hard to replicate. Then you diversify to kind of make your portfolio more secure. Then you uh build a platform so others can build on it, and then you uh build a team with ownership mindset, and finally you uh invest in research and development to kind of build the next generation of uh your product or services before your competitors spread.

2:44 SPEAKER_01: Right? Now your company and your product is very much like mine, like you are a CTO, uh, you know, my consulting firm is primarily an advisory as a fractional CTO. That that's my primary mode of consulting. So, you know, we we are we are very similar in that way. Uh so talk to me about you know your uh how you got started uh as and uh you know what you do for your client and you know for with your own consulting, uh what's the vision? But let's start with the beginning. Like when and how did you realize that you know you want to be a CTO and this is where you can provide uh you know companies the most value?

3:33 SPEAKER_00: It's interesting because I never knew that I wanted to be a CTO. When I was I was very lucky at an early age, we had a computer in the house. My generation is kind of the first generation that didn't have computers when we were super young, but as we got older, computers started to be pretty everywhere. And I was pretty lucky as a middle schooler to have a computer in the house. I took to it pretty well. I was able to understand it. I was creating databases and all that kind of good stuff using floppy disks and everything that came along with early DOS-based computers.

4:08 SPEAKER_00: When I went into look for a job, I was working for a media company. Uh, the Palo Alto Weekly was the newspaper. And my boss came to me and said, Hey, you kind of seem like you understand this computer stuff pretty well. Do you want to do it part-time for the company? Because we're going to hire somebody anyway. So I took that opportunity to split my time between the journalism and the design work I was doing and build a repertoire of understand of understanding the technology that was important for running a newspaper.

4:40 SPEAKER_00: And that kind of blossomed over the years as the internet came on. We were the first internet, we were the first company to publish our entire editorial content to the web. And that was in 1994. So this was pre-Google, pre-Yahoo, pre-browsers in a lot of sense. So we were into it very early, and I had my fingers in all of that. As time went on, the company grew. And as that grew, I needed help. So I was moved into a computer administrator role. There was nobody above me other than the CEO. And then ultimately to the CTO role, where I had a staff under me.

5:17 SPEAKER_00: We ran multiple websites. We had an ecosystem of infrastructure internally that was running everything from our circulation system to our ability to take payments for our users and our websites. Fast forward, I left that company about a year ago, actually, almost exactly a year ago, to go work for a client of mine. And this is somebody who I'd known for almost 20 years. He's a serial entrepreneur. And every time he started up a company, I'm like, hey, is this the company you're gonna come hire me for?

5:50 SPEAKER_00: And he's always like, no, no, no, keep with your sure thing. He came to me about a year and a half ago and said, This is the sure thing. I think that uh ProLegal is going to be the company that will go everywhere. And I want you to come work for me as CTO. So I left my job of 32 years and went to go work for ProLegal.

6:11 SPEAKER_01: So, you know, uh it's it's interesting that you know you were kind of there at the right place at the right time. So it just kind of you know worked and naturally for you. So describe to me transitioning from a media industry where you know you had like business knowledge and you had worked like you you were like a journalist, right? To going into legal industry. Uh, you know, of course, technology is technology everywhere. Uh and you know, like I believe every company today is a technology company.

6:43 SPEAKER_01: So but you know, making the transition to a different industry, what were you able to kind of reuse and what were some of your new learning curves?

6:53 SPEAKER_00: Sure. So I mean, you're right. Technology is technology. I mean, and every company is a technology company, whether they realize it or not. At the media company, it was dragging a lot of the people into the technology world. I mean, not so much in the last decade or so, but early on, you know, we put computers on people's desks and they were like, what am I supposed to do with these things? So it was it was the training of and making people understand that the technology is here to help your job be easier, not to make it be harder.

7:22 SPEAKER_00: And if it's harder, then we're doing something wrong. And that's kind of the thing that I have always taken away from how I work is that the technology should be a tool, not a cry, uh, not a um hindrance. And if it's a hindrance, then the problem is with the technology. So the transition from the media company to the law services company is not that big of a difference. At the end of the day, we still have a database, we still have users that have to access those that information, we have files that need to be filed, we have infrastructure such as internet and um VPNs and all those sorts of things that all need to happen.

8:04 SPEAKER_00: I think the biggest thing that I understood as the biggest change in the last five years, six years is the remote work aspect of it. And we were not set up as a media company when COVID hit to work remotely. Luckily, I had seen the writing on the wall and we I kind of knew that things were going to go the way they were going to go, and we'd be shut down. I didn't think we'd be shut down for as long as we were, but I put things in place so that we could work remotely. Uh, and that whole infrastructure is something that served the organization very well.

8:41 SPEAKER_00: And when I moved to ProLegal, we have both near shore and offshore users, internal users, that need to be able to access stuff internally to our network. So it's the same kind of problem, just in a different setting. And so, as far as what the tools that we build do, it's kind of the same thing, right? It's it's the tools that both internal users need to use and external need users need to use. In the case of media, it's people reading stories or watching videos or interacting with reporters. In the case of the law services company, it's people needing funding.

9:18 SPEAKER_00: It's people that are looking for rides to get to their medical appointments. And it's the law firms to be able to build websites and programs that will allow them to find new clients to grow their business.

9:33 SPEAKER_01: Yeah, yeah. I I agree. Like, you know, all of those concepts they kind of carry over. Like every industry kind of has its own setup compliance, right? And those are things that uh kind of differentiate from industry to industry, other than that, the technology is the same, right? Right. Uh but like, you know, outside of these uh, you know, uh, you know, clients of yours that you work for, you have your own company, uh, Bravo IT consulting, right? Um is is it purely for service purposes, accounting purposes, or are you building something in-house that you think can uh service all your clients?

10:14 SPEAKER_00: Yeah, so I look at my Bravo IT consulting as a extra kind of side project. Um, at some point I thought maybe that would be the route I would go and and leave the paper for that. I have a pretty I had a pretty good stable of clients that I was working with, everything from small businesses to medium-sized businesses to the little old lady who needs help with her printer. So it was really meant more as an outlet to be able to do things that I couldn't do within the normal CTO job at the media company.

10:47 SPEAKER_00: And out of that grew the my podcast, the Your Tech Makeover podcast. When COVID hit, I couldn't go see all these people. So I was doing Zoom calls, and I thought, you know, instead of doing Zoom calls one-on-one with somebody, why don't I do some way that I could educate or answer questions that I know people are having in a bigger format? So I kind of dovetailed that onto my consulting business to be able to help people understand the technology that's not really business oriented, but just their normal everyday technology.

11:22 SPEAKER_01: Yeah, yeah, that's cool. Like Andy, you you you are a fellow podcaster as well. I mean, we have uh so many things in common, right? So uh, you know, how how do you kind of connect, like, you know, you still do your podcast and you still have the consulting? Like, is it somehow complementing your uh work? Because you know, uh, I'm coming to like my next stage of question, which is like, you know, I always say that, you know, no matter what you're good at, just like you, I have my own consulting. You know, my private expertise is in the cloud at AI because of my Microsoft background.

11:58 SPEAKER_01: But, you know, I also have a podcast, I do a lot of social media, I I speak at conferences, uh, you know, I own a travel agency. I believe that, you know, no matter what you're good at, you can't like count on that for everything. You have to diversify, you have to build businesses which are tangentially similar to your business, but also supported, right? So you have a few things like you know, your own business and podcast, like you know, how are they supporting your business or do you feel like it's uh distraction?

12:31 SPEAKER_00: Yeah, so I mean, I they all kind of work together because in my normal, you know, I'll call it my W-2 job at Pro Legal, I'm able to build tools, I'm able to be out there as the expert in our company of um, you know, these are the kind of things that law firms need to look for in technology, and and we can help you get there. In my CT, I'm in my uh Bravo IT consulting business, it's kind of the same way, just on a smaller level. It's the 20-person business who is looking for a new way to run their bookkeeping and they they're looking for a solution, or it's a company who's moving and they're moving into a totally shelled space and they need internet and infrastructure built for it.

13:19 SPEAKER_00: So it's a way that I can still do things that I can't do in my normal job. And I like interacting with individuals as well. The other part of it is the podcast, which really dovetails more onto my consulting business because it is really the same kind of information that I give in that one-on-one treatment I try to give through my podcast. So they all are symbiotic of each other, uh, although my CTO job is probably the one that's different than the other two.

13:53 SPEAKER_01: Yeah, yeah. So I mean, I agree, and like, you know, I am kind of along the same way, right? My uh my speaking kind of helps me uh you know establish myself. I wrote a book. The book is, you know, um another channel where uh people can get to know me. The podcast helps uh you know build relationships and it kind of gets people to know how I think, right? Uh and and they all kind of help attract customers for my core business. And then you know, I have a travel industry that feels I need to travel for my business, so it kind of helps get a good uh travel deal, right?

14:34 SPEAKER_01: So they all kind of work together to support the core, which is uh consulting. And down the line I might build more products that that would also help kind of accelerate the consulting, right? You know, we also talk about uh like building a platform, right? So you're not building any product, but like have you what have you?

14:57 SPEAKER_00: We are building product. I mean, so so for ProLegal, we are building, we have built a suite of products that law firms can join in order to interact with their clients, interact with the services that we offer. So, so I have, I mean, that is kind of the baseline of what we're doing at ProLegal right now is we're building this product that will go out to the market and users will be able to use it. Like, for instance, we just launched ProLegal Talent, which is a talent services site for people looking for jobs at the law firm space.

15:35 SPEAKER_00: There's plenty of places to go out and find jobs, but there's nothing that is targeted to law firms. So the idea is that law firms are always looking for talent. They would come to us and say, we need a paralegal. We would then go out and find that paralegal. And where our difference is, is that the technology in the background will find a good match for that person and it's concierge-based. So we are actually giving them not a hundred people that potentially could fit their job, but two people that we know is going to fit their job.

16:11 SPEAKER_00: So, so, and at the paper, we did kind of the same thing. When we started, there was no WordPress, there was no CMS systems. So my partner and I, we built up the CMS system. And had we been smart, we would have marketed it and been the WordPress of the day. And that system ran until the mid-2020s. And it it is building that those tools and those that infrastructure, and basically that product. While in the case of the paper, we weren't selling it. Um, it was an internal product. But in the case of ProLegal, we absolutely are on the external side of it.

16:48 SPEAKER_01: Okay. So so ProLegal is not a law firm by itself. It it provides service for legal industry.

16:59 SPEAKER_00: That is correct. Yeah, yeah, yeah. So we we are not a law firm. We don't have lawyers in-house. We don't have, you know, we we can provide services to law firms, and we do provide services to law firms. We can provide support to those law firms. So if they're looking to write a brief, we have people who we could go to to say, you know, this is what we're looking to do and provide that service for them. But yeah, we are not a law firm. We do not go out and and have clients that are uh looking to sue people or or are plaintiffs and such.

17:32 SPEAKER_01: So that's a platform. That's a platform that that you know law firms and people who are seeking law and lawyers or uh legal advice could uh connect for that reason. That's interesting. Like how much of it is AI? Like, you know, nowadays, you know, the there is this big craze about AI lawyers that you can you know uh get legal advice through AI, right? Uh do you have any kind of AI offering within your service? Is that kind of a uh you know of seen as as negative by your client because you know they might say, you know, if your AI is doing that, you know, we'll lose client, right?

18:16 SPEAKER_01: So you see that.

18:18 SPEAKER_00: Yeah, so we we when we launched the ProLegal Suite back in January, um, we had ProLegal AI and it was built such that it was to be trained on legal services, to understand the law, and to know how a lawyer would write, you know, and be able to have a conversation with a lawyer to understand their cases. What we found was that there are services that were either more advanced or the law firms had stuff already in place that they weren't looking to make a change for those sorts of things. ProLegal, we use AI all the time, and we use it as a tool to help us understand, you know, is a case that we're gonna fund something that is a good case, you know, does it have all the right pieces?

19:07 SPEAKER_00: And we've trained our own internal AIs to be able to understand those things. As a developer, I use AI all the time, and we are building tools way faster than we could have done if I was just writing code or if we were just writing code internally. But none of that code gets pushed live without review. I I am a stickler for knowing that AI is a tool and it does really well, but it also does really badly. And we are just really confident that we can build things quickly with AI, but we're not confident in the AI that I'm just gonna allow anybody to push anything live.

19:46 SPEAKER_00: So I think that's where businesses fail so often is that they think that AI is the end all and be all, and they just let it run rampid. And what you end up with is a bunch of bad software out there and a bunch of tools that are not really built for the user at the end. It's a lot of extra code to do something that should be very simple.

20:09 SPEAKER_01: Yeah, yeah. So so like you know, besides the connecting lawyers to uh you know uh clients, have you done anything on the operational side, like document extraction, you know, identifying the legal flags, you know, uh generating uh, you know, proposals? And uh are any of those types of AI services you're offering to lawyers?

20:34 SPEAKER_00: So we're not offering them to lawyers, although we do use them internally. So a big part of our business is funding on a lien. So if somebody were to get in an accident and they have a judgment coming their way, they may need cash up front. So we offer it as a lien against that payment that is coming from their judgment. And what we need to do is understand is this how much can we fund on this case? And so we've built our internal AI to be able to take all the documents that go along with a personal injury case and boil it down to, you know, is this case something that is going to be successful?

21:15 SPEAKER_00: And what are the what are the payments potentially going to be like to give us an idea of this is how much potentially we could loan to this, and loan isn't the right word, advance to this customer to be able to help them through a hard time because they were in this accident. So while that's not forward-facing, it's definitely something that we use internally to run our business to understand how to help our clients.

21:42 SPEAKER_01: Okay. Yeah, yeah. I mean, that that makes sense. Now you are using AI on the internal side, you know, maybe down the line you'll expose it to the lawyers or absolutely your clients, right? Um no l let's talk to, you know. the operation side within your company. Now you are the CTO for Pro Legal. Correct?

22:05 SPEAKER_00: Yes.

22:06 SPEAKER_01: How how much of authority do you have within the org chart to build your team and how do you incentivize your team to uh you know kind of think and act like with an ownership mindset? You know, how are the teams incentivized to start new product, uh start new project and improve existing project and you know how how is the leadership getting selected from you know people who are new and are building something new and are able to scale it, right? Can you throw some light on that?

22:43 SPEAKER_00: Sure. So our organization is pretty small. We're only 15 total people. I have one person who works for me full time. I have a couple of other people that are contracte. I have ultimate authority over the technology. The the beautiful thing about the CEO is that when he hired me, he said, Frank, think of ProLegal as your company. Think of make it good for what you think this company should be. And don't let other people tell you you can't do certain things. And that's a freedom that while I enjoyed my time at the media company, I never had that kind of autonomy.

23:20 SPEAKER_00: It always had to be a committee and groups of people getting together deciding how and what we were going to build. And to be able to have full autonomy, I mean ProLegal Talent is a great example of that. It was me and another coworker having a conversation about our own internal hiring and I said, you know, wouldn't it be cool if we were able to do this on a macro scale for all the law firms that we support. And we went from idea to concept to build to launch in less than two and a half months.

23:54 SPEAKER_00: And that is really what we've tried to do internally at ProLegal to be able to give everybody agency to say, hey, you know what? I have an idea and come to me and say Frank, I want to build this into our own CRM system or I want to build this external tool. And obviously we then have to decide you know where do we want to put resources, what is the most important thing at the time but everybody has that ability to say, I want to do X and I think that it's a good idea because of this. And no good idea, actually no idea is ever just pushed aside.

24:31 SPEAKER_00: They are always vetted and the really good ones are built at a very high rate so that we are able to get to market with those ideas because we have somebody internally that is champion championing that that idea.

24:45 SPEAKER_01: Yeah yeah that that's excellent. So let's talk about the innovation right the technology I I believe you know uh at the final stage you know that you need to invest in RD and you need to uh kind of push the boundaries and create the next best thing yourself before your competitors create, right? So out of all the things like imagine you have unlimited funding right what do you see are some of the areas of improvement and some of the things that you know like requires more research. So if you could invent something new within the legal industry or within you know IT consulting industry, where would you uh invest in research and development and what would you create?

25:33 SPEAKER_00: I mean not to give away the secrets of the stuff we're working on of course I think that a big hole in law firms is their ability to manage their information. A lot of law firms whether they be super small or really large they have they are really good at the law. And that's a good thing because we need them to be really good at the law. They as a general rule are not necessarily the most organized group of users. So it would be amazing to have a tool that can take their loss firm basically and run it and and we've thought about different ways to potentially help law firms do that everything from a uh you know a a two-person law firm where you have a paralegal and a lawyer to a law firm with hundreds and hundreds of people the problem is still the same I have this information I need to be able to get to it I need to be able to understand what this information is depending on the type of law I might need to be able to build that client.

26:43 SPEAKER_00: So you have all these same kind of problems it's nothing revolutionary because there are tools out there that do this. It's just in our mind none of them do it very well. So that is kind of a big greenfield that we're looking at as a way to help law firms further run their businesses. And if we can then tie those into the services that we already offer, such as the Rides tool and the talent tool and the tool to allow us to take intakes and manage their marketing and such, then that's a win for the inf for the whole organization and the whole type of business as a whole.

27:21 SPEAKER_00: From my consulting side, I look at it more as where can I bring value to incremental things? Like I'm working with a client right now who is a solopreneur that is looking to have a fiduciary service and she needs everything. She doesn't understand the the the marketing side of it. She doesn't understand the email data side of it. And I'm kind of helping her walk through those things. And and again not to bring it back to the podcast but your tech makeover does kind of try to do that same thing on a very basic level of, you know, I I need to understand how do I organize my documents?

28:02 SPEAKER_00: That is something that whether you are a CEO of a multi-billion dollar company or a person who is trying to manage their own files um they need to understand what is cloud drives and how do they work and how do they all work together? And if there was a way to bring everything together and make it easy for somebody, going back to your question about what would I invent, I would invent that because that does not exist as far as I can tell.

28:30 SPEAKER_01: Yeah yeah I mean it probably exists like you know in a disparate way but it's not very unified. It's not seamless and it's not the way you would want to want it to work, right?

28:43 SPEAKER_00: Yeah I mean a great example is is this person is using iCloud because she has an iPhone and she is using OneDrive because she has a Windows machine and she has iCloud and OneDrive installed on the machine and she has files everywhere and she's like I don't know where anything is because nobody has made it easy to make everything be in one place.

29:05 SPEAKER_01: Exactly exactly because you know every vendor is trying to kind of you know lock them in into their own proposition yes yeah so you know uh coming to that like you know how do you see you know open source and open standard as a way uh for innovation like legal industry understand like that there are a lot of compliance there like are they open to putting stuff in the cloud? Like are they open to using open source or are they open to kind of releasing their standards as an open standard and are they open to contributing to open source or releasing their platform as open source?

29:47 SPEAKER_00: Yeah you know I mean I think that historically law firms are they'll do whatever's easy sometimes so they may have somebody on staff that says yeah let's dump everything into a Google Drive and not necessarily think about you know what are the ramifications of that? What is the ramifications of somebody gaining access to somebody's account and then ultimately being able to get into our case files. That's where a lot of these off the shelf I'll say systems come in and they try to unify these things.

30:20 SPEAKER_00: Some of them do safe stuff in the cloud some of them you need internal servers to do that which in 2026 that just blows me away that there's not a way to do some of the stuff they're doing without internal servers. I I am a huge open source type person. I mean my my my technology is free good free software is better than a very expensive piece of software but I'm not afraid to pay for a piece of software either. And I think that open sourcing the technology behind it to let other people be able to build on top of other things is an important piece of it.

30:56 SPEAKER_00: Now if I were to build a tool that does everything that we talked about, would I open source it? Probably not but I would want to make sure that there were standards so that people can get from what we've built to some other system. And I would hope that that other system would build tools to be able to move from their system to ours. So I think that standards are super important and to be able to interchange data is a very important piece of it.

31:23 SPEAKER_01: Yeah yeah so so uh talking about standards uh you know another big piece of you know kind of s securing the future once you get to the top is managing external environment, right? So for any regulated industry, one of the big parts of managing external environment is regulations and policies and you know there might be common standards that exist. That's on one side the other side is user education right you know letting people know that there is a service like this that can uh do this so you don't have to do things the old way right so how much uh you know how much of your time or you know what's done within the company on both sides to uh on one side making sure the regulations are uh kind of done in a fair way so that your uh business is uh you know not difficult to run uh what is being done on the user side to make sure to educate users that uh they don't need to do things the old way you know here is a service that they can use that kind of you know that would help them and it's you know better for the overall industry.

32:38 SPEAKER_00: Yeah I mean standards and education is kind of the biggest thing of any product. I mean I I know that a lot of what I do is educating users to on how to use the technology. I mean I spend a lot of time thinking about if I build this tool a certain way, can somebody understand it? And that goes beyond the UI UX, but does the process make sense? So I think that's a very important piece of it. And as far as regulations go, the funding business that we're in is highly regulated. And we need to make sure that in every state that we are doing the right thing.

33:18 SPEAKER_00: So we have lots of different pieces that are going on both in the forefront and in the background that we're having to keep track of regulations and everything we go to release, we make sure that our terms of use and our privacy policies match the regulations and are able to be understood so that ultimately we don't get in trouble for doing something that we shouldn't do.

33:42 SPEAKER_01: Okay.

33:42 SPEAKER_00: Yeah, yeah of course.

33:44 SPEAKER_01: Now finally we are nearing the end of our podcast is there anything big big launch or something happening on the pro legal side or on your side that you would like to announce on this podcast?

33:59 SPEAKER_00: Yeah so I mean the the launch of ProLegal Talent is probably the biggest thing that is happening. It literally happened uh this week I don't know when this will air but you know it was something that that like I said we we worked really hard on it and we think it's a really good platform and we're we know that it is a hole in what law firms need. On the on my own personal side of things I have a couple of projects that I'm working on. I can't talk about any of those yet but they are they are also exciting and and it's using it's reusing technology that I have always been a fan of and I think that it's a cool tool that will allow people to do something that they weren't able to do before.

34:42 SPEAKER_00: And then for for your tech makeover that comes out every other week um there's always new topics. I'm always looking for new topics questions that people have so you know it it's found at your techmakeover.com and it's really a simple small bite-sized 10 to 15 minute episodes talking about a particular technology.

35:04 SPEAKER_01: That's great. I will be sure to mention that okay um so with that we are at the end of the episode. If this episode shifted how you think about AI in your organization send it to one person who needs to hear it. And if you're ready to act visit tipsora.com to get certified or reach me directly at arnancipating.com The intelligence economy is already here the question is whether you are building for it. That's a wrap on today's episode of What Comes Next. If this conversation gave you a new way to think about AI strategy, share it with someone who needs it.

35:43 SPEAKER_01: You can find everything I'm building at tipsura.com including AI certifications for you and your team connect with me on LinkedIn by looking up my name Arnan Chipatnaik you can find Frank on LinkedIn or you can visit his website bravoitc.com until next time build the architecture and the advantage follows